[Mg].C(COCCOCCOC)CCC.II.BrCCBr.[CH:21]1([CH3:31])[CH2:26][CH2:25][CH:24]([CH:27]([CH3:29])[CH3:28])[CH:23](Cl)[CH2:22]1.[C:32](=[O:34])=[O:33]>>[CH:21]1([CH3:31])[CH2:26][CH2:25][CH:24]([CH:27]([CH3:29])[CH3:28])[CH:23]([C:32]([OH:34])=[O:33])[CH2:22]1Magnesium (37 g, 50 mesh), butyl diglyme (600 g), and iodine (0.1 g) were added under nitrogen to a 1-liter flask equipped with agitation, addition funnel, off-set adaptor for thermometer, gas addition tube, and condenser. The mixture was stirred for 30 min. at 90° C., and then 1,2,-dibromo ethane (2 cc) was slowly added. p-Menth-3-yl chloride (200 g) was then added at a rate of 50 g/hr (0.32 mole/hr). After approximately ½ of the p-menth-3-yl chloride was added, carbon dioxide was concurrently added by bubbling the carbon dioxide into the mixture at a rate of 15.91 g/hr (0.36 mole/hr), and at a temperature of 90° C. Addition of the carbon dioxide was continued at a temperature of 90° C. until 30 min. after all of the p-menth-3-yl chloride was added. After carbonation was complete, the resultant mixture was hydrolyzed with aqueous hydrochloric acid (1:1 hydrochloric acid/water), and the resultant oil layer was neutralized with trisodium phosphate. VPC analysis showed a yield of 93.18% by weight of p-menthane-3-carboxylic acid.
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